What to do. Where to go. When to do it.
mobile menu trigger

Road Trip Around the Coast of Maryland

Road Trip Around the Coast of Maryland

Take a Trip on Your Own Terms With Your Own Tribe

Good news. The coast isn’t canceled. Summer may be officially over and school in session, but—wait for it—that session is Wi-Fi-enabled. So while your work-school life lingers virtual, your real-life just got more flex. Zoom over to Worcester County with the fam, and take that next Zoom sesh with a view—then turn the historical Maryland coast into the classroom of life. Couples (those sans minis or parents) in need of an escape from the kids can rendezvous romantic-style as they roll up and down the coast of Maryland basking in the sweet autumnal breeze, sightseeing, and sailing before rounding out the romantics with a pitstop for some alfresco seafood. Ah, sweet escape.


You’ll find all levels of affordable accommodations around Worcester County, from luxe resorts and brand hotels, to intimate B&Bs, award-winning campgrounds, fam-friendly rentals—and even Fido-friendly ones to book.

Across the Worcester County hospitality industry, every venue and accommodation is working hard to ensure every guest is staying in clean, sanitized rooms with social distancing and safety guidelines followed. Here are a few of our favorites from the plethora of places to post up in Worcester County.

Change the location of your classroom (and office) and live the resort life at Francis Scott Key Family Resort in Ocean City. The fam-friendly atmosphere is located 1 mile from the beach and boardwalk (lunchtime phys ed, perhaps?) and provides nearby access to a free county boat ramp for your fishing excursion or evening relaxing on the water. And whether you’re looking to uproot the crew and live the login life beachside or microcation away for the fam, this resort has you covered. Think options from small two-person selects to large six-guest spots, and basic amenities to well beyond with full kitchen-equipped cabins and rooms, and everything in between.

For those seeking solitude or just being one with nature, there are plenty of wild and wonderful au naturel options like Assateague, Pocomoke River State Park, and many more. At Assateague Cottage in Berlin, turn down for relaxation. Swap the tent for a comfy cottage on Assateague Island, and channel Walden as you retire to relax among comfy linens and a good book. Be lulled to sleep by dulcet island sounds against the salt- and campfire-scented air, setting you to awaken well-rested, refreshed, and at peace. For more real-life learning options at your “doorstep” after a long day of e-living, families will enjoy the outdoor-activity paradise that is Pocomoke River State Park (more on this below).

If you’re looking for a more intimate escape, B&B options abound. Situated on the ocean in Ocean City, The Inn On the Ocean is the perfect blend of hospitality, luxury, comfort, and beauty with magnificently appointed rooms for you and your significant other to escape to. Sip your morning coffee as you watch the waves go by from the oceanfront veranda; take a lunchtime drive to Assateague Island; and, after work, enjoy nearby fishing, watersports or just take the day off for 18 holes of leisure and some wine tasting.


2020 has deepened our appreciation for the great outdoors. Lucky for you, this charming beach town boasts plenty of fun outdoorsy options. And when your office is a coastal paradise, play options are aplenty—on the shore and beyond: think fishing, hunting and crabbingsurfing, sailing, kayaking, SUPing, and watersports galore; horse trailsgolfparks and so much more.

For watersports lovers, paradise found indeed in Ocean City at this paddleboard HQ. Test your SUP (stand-up paddleboarding, natch) skills with Walk on Water Paddle Board. Known aptly as W.O.W., the SUP co. offers lessons, rentals, SUP Yoga, and more with a wide variety of paddleboards and gear for you to purchase once you’ve decided to just set up camp and stay in Worcester forever.

Then, not only can wild horses not keep you away—they are one of the top reasons you should be booking your family getaway to WC. Live on the edge for some super-safe socially distanced fun on the naturally beautiful and untamed Assateague Island, best known for herds of feral horses running free. Here, your education-ready moment awaits, situated just over the bridge from Ocean City, in this postcard-perfect barrier island—occupied by the island’s most famous four-legged residents freely grazing grass and splashing about in the waves since the early 1700s. Your minis can learn everything equine while you take in the pristine beaches and Assateague Lighthouse and then wander together in wonder along the 37 miles of salt marshes, maritime forests, and sandy beaches, or via paved or unpaved trails on foot, bike, or horseback.

And whether you decided to camp out at Pocomoke River State Park or stay “inn,” either way, you will want to take in this scenic spot. Shad Landing in Snow Hill and Milburn Landing in Pocomoke City bookend the setting of this park, set against the scenic Pocomoke River on 15,000 wooded acres of Pocomoke State Forest in the Southwestern section of Worcester County. The unique combo of swamp and upland offers visitors the chance to view a variety of plant and animal life, with great fishing waters and much more.



Refuel with some safe and socially distanced family (or date-night) reduced capacity selections at a slew of shore-town staples with outdoor seating areas, including breweries and wineriesfarm-to-table (and dock-to-plate) sup spots, and even farmers markets fresh a farm-fresh dinner at home.

Your family will be hooked on fresh, delicious fare from Hooked’s Coastal Style magazine 2018 best chef, Christian Costantino, at this fam-friendly Ocean City fave by Off the Hook Restaurant Groups. Costantino’s creative culinary masterpieces are available for dine-in (indoors or out) or carryout—but either way, you’re gonna wanna make time for some island vibes and a happy hour at the Tiki bar.

For over-water sunset views and culinary masterpieces of land and sea, Tailchasers Restaurant & Dock Baris where you will want to be. Nestled on the canal on 122nd Street in Ocean City, the family restaurant, also by Off the Hook Restaurant Groups, offers indoor and outdoor seating and online ordering to meet you and your family where you are.

Or, adult-only field-trippers can brew up some fun and serious beach vibes at Backshore Brewing Cowhere fall is on tap with the return of its award-winning pumpkin ale, Fist Pumpkin (think notes of graham crackers, pumpkin, brown sugar, and cinnamon—basically fall in your mouth). Brewed in the salty air, Backshore’s beers pair perfectly with its Margherita pizza and a post-nosh stroll down the Boardwalk. Peep its brew cams to watch these frothy creations made live or to scoop views of the Boardwalk.

And if wining and dining at your home away from home is more your speed, the beach town markets are a must-stop shop. Ocean Pines Farmers & Artisans Market is open year-round at White Horse Park. And, situated in Budget Travel’s recently voted coolest small town in America (no big deal!) you’ll find Berlin Farmers Market, open to masked customers on Sundays through September from 9 a.m. to 1 p.m., with a special senior shopping time (8:30 to 9 a.m.).

So, if you’re not already packed and in the car rollin’ down the highway toward a much-needed change of scenery and safe family getaway, just remember, we are meant to do more than exist. So slot those WFH hours while your mini e-learns shoreside—and make Worcester County your “virtual” classroom and playground… and the best memory of your year! See you along the coast!